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Asymmetric Total Synthesis and X‐Ray Crystal Structure of the Cytotoxic Marine Diterpene (+)‐Vigulariol
Author(s) -
Becker Jochen,
Bergander Klaus,
Fröhlich Roland,
Hoppe Dieter
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704678
Subject(s) - diterpene , total synthesis , salt metathesis reaction , stereochemistry , metathesis , chemistry , key (lock) , ring (chemistry) , computer science , organic chemistry , operating system , polymerization , polymer
A crystal from the China sea : The asymmetric total synthesis of (+)‐vigulariol (see picture: red O, blue C, white H) has been accomplished in eight linear steps starting from ( R )‐cryptone, which is readily available from eucalyptus oil. Key steps involve an asymmetric homoaldol reaction of chiral allyl carbamates and THF cyclocondensation. Ring‐closing metathesis led to the tricyclic framework of the cladiellin diterpenes.